Microwave-assisted synthesis of benzenesulfonohydrazide and benzenesulfonamide cyclic imide hybrid molecules and their evaluation for anticancer activity

Abstract

4-Methyl benzenesulfonohydrazide (1a) and 4-methoxy benzenesulfonohydrazide (1b) on condensation with furan-2,5-dione, hexahydroisobenzofuran-1,3-dione, 3a,4,7,7a-tetrahydroisobenzofuran-1,3-dione and isochroman-1,3-dione under microwave irradiation condition gave corresponding condensation products 2a,b; 3a,b; 4a,b and 5a,b, respectively, in good yields. Microwave-assisted condensation of 4-amino-N-(thiazol-2-yl)benzenesulfonamide (6a), 4-amino-N-(pyrimidin-2-yl)benzenesulfonamide (6b) and 4-amino-N-(4-methyl pyrimidin-2-yl)benzenesulfonamide (6c) with furan-2,5-dione, hexahydroisobenzofuran-1,3-dione, 3a,4,7,7a-tetrahydroisobenzofuran-1,3-dione and isochroman-1,3-dione gave corresponding condensation products 7a-c, 8a-c, 9a-c and 10a-c, respectively, in good yields. All these compounds, i.e., 2a,b; 3a,b; 4a,b; 5a,b; 7a-c; 8a-c; 9a-c and 10a-c, were screened for in vitro anticancer activity against five human cancer cell lines, i.e., breast (T47D), lung (NCl H-522), colon (HCT-15), ovary (PA-1) and liver (Hep G2). Compounds 7c and 9c exhibited good anticancer activity against ovary (PA-1) (IC<inf>50</inf> value 8.12 ± 1.83 ?M) and liver (Hep G2) (IC<inf>50</inf> value 4 ± 1.9 ?M) cancer cell lines, respectively. © 2015 Springer Science+Business Media New York.